How to Make a Real Connection with Someone: Part 1

How to Make a Real Connection with Someone: Part 1


If you’ve read any of my articles or eBooks, you’ll know by now there are 2 things I recommend doing above anything else in online dating:

1)   Asking questions about who someone is and why
2)   Sharing specific detail about who you are and why

Do this in first messages, do this as you continue to message or text, do this on your profile, and do this on a first date.

For a long time, I thought this obsession with asking/being asked questions was unique to me – that this was the only way I felt comfortable getting to know someone, or having them know me.  

It’s incredibly important to me that my partner – friend, date, long-term significant other – ask me questions, be genuinely interested in my answers, and have a willingness to share openly in return.  Curiosity and self-disclosure are the foundation (or at least the key building blocks) of my closest relationships.

This has also been the biggest running theme for why I’ve ended relationships.

When someone is not curious about me, or doesn’t seem to know how to be curious, and share who they are in return, I don’t feel we can grow our relationship together.

This really hit me over the head recently, prompting me to examine this universal need for creating connection with others.

I was in bed with a new “man-friend.”  

We’d met on Bumble and for the past several weeks, we’d been sparking with chemistry.  Our rapid-fire banter made both of us feel like hilarious geniuses, we shared an electric need to touch each other, and had that insatiable need to stare at each other’s faces in delight/fascination/lust.

But I knew I had to end it. 


After all that banter, he did not seem to give a fuck about my thoughts and opinions about things that matter to me most:

Why I chose to start my own business, what I thought of my parents’ ongoing divorce, how I feel about guns and politics and religion, what I want out of the next five years of my life, or why I experience intermittent insomnia.

How did I know he didn’t care?  Technically, I didn’t.  But what I did know for sure was that he didn’t ask me about any of those things despite me mentioning each one specifically. 

In his defense, I didn’t volunteer my own feelings or thoughts, either.  This is a little test I run (for better or worse) to see how much someone really wants to know who I really am inside my head (the stuff that remains after you’re old and ugly) by mentioning something important and seeing if they ask about it.

I was also open to the fact that his strategy for getting to know someone was just different from mine.  Maybe he is observing my actions and then he’ll confirm his impressions of me with me later, I thought.

So, that last morning in bed, I asked him, “How do you like to get to know a person?”

He paused for a long time. (Uncharacteristically long; he’d always been quick with a quip.)

“I don’t know,” he said.

“Well, for example,” I led, “I like to ask someone questions to learn more about their thoughts, opinions, and feelings.”

He was quiet again.  “I’ve never thought about it.”

That’s when I knew it was over.

Several years ago, I might have spent more time leading by example, trying to show him how we could ask deeper questions, have more engaging conversation, and share who we really are with one another.

But recently, I’ve decided to focus on building strong foundations with those who already value this practice from the start of our relationship.  I now need at least some of this as raw material to start with.

Learning that he’d never thought about how he likes to – or tries to – get close to someone was a deal-breaker for me. 

To me, real connection – an honest, vulnerable, curious, non-judgmental desire to understand why and how someone else is in the world – that connection we make with others is what makes life worth living.

When we seek to understand someone else’s perspective, feelings, ideas, motivations, fears, opinions, and thoughts, we can really love them for who they are.

When they try to do the same for us, they can love us – and we can make great partners in all walks of life: friendship, romance, business, the community.

This is the goal, right?  We all want to be seen, heard, and loved.

While this has been a theme in why I’ve ended relationships, it’s also been the predominant quality of my strongest, most lasting, most joyful relationships.

I’ve been doing a lot of research around this, and I now know it’s not just me. 

Our need for social connection is hard-wired as a species. 

Our brains, specifically the neocortex, are bigger than other species’ because of our need and ability to socialize. 

Our bodies were built to help us connect with others – to vocalize, touch, and chemically bond with each other.

The big question is always: how?

How do we learn to connect better given our circumstances – in our world of apps, Snaps, texting – that have arguably dulled our ability to be casually open and naturally vulnerable with each other? 

More specifically in dating / online dating:

What do you say on Tinder or Bumble to make a girl more likely to want to talk to you – share who she is, and learn more about you, specifically?

What do you do on a first date to demonstrate you’re genuinely interested in learning who she is on a deeper level? 

What is too much, too little, and just right to ask, and to share about ourselves, when we want to have a real chance at real love – and not be back home and swiping again by 10pm?

These are some of the questions I’m going to start answering on MenAskEm.  As always, I’ll try to share the research, and tactical and actionable next steps with you.  But I hope you’ll enjoy the philosophical aspects of this new conversation too.

Thanks, as always, for being one of the good guys who get why this is so important to do, despite it being weird and difficult at times.  (Because if that isn’t love in a nutshell, what is?)

Love you guys.

P.S. Part 2 is out!  Read it here.